Hydrochloric Acid → 1-N-Ethoxycarbonyl-4-(2-amino-4-fluorophenoxy)-4-ethynylpiperidine
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:23]#[CH:24])([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[N+:20]([O-])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].CO.Cl>O.[Fe]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[NH2:20])([C:23]#[CH:24])[CH2:10][CH2:11]1)=[O:5])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 22.3 g of 1-ethoxycarbonyl-4-ethynyl-4-(4-fluoro-2-nitrophenoxy)piperidine in 535 methanol was added 37 ml of concentrated hydrochloric acid in 150 ml of water. To the stirred mixture was added 78.6 g of iron (reduced, electrolytic) in aliquots. The reaction temperature rose to 45°. The reaction mixture cooled to ambient temperature over 1.5 hr. The mixture was poured into water/ice/sodium carbonate solution, extracted with dichloromethane, washed with water and saturated sodium chloride solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of solvent provided 20.2 g of an oil. An aliquot of 10.0 g of the oil was dissolved in ether and filtered through 200 g of alumina and the filtrate was evaporated. The residue was dissolved in 10% methanol/dichloromethane, filtered through 200 g of silica gel, and the filtrate was evaporated to provide 8.6 g (84.7%) of product, as an oil.
Workup
- customrose to 45°
- extractionextracted with dichloromethane
- washwashed with water and saturated sodium chloride solution
- dry with materialdried over anhydrous potassium carbonate
- filtrationFiltration
- customfollowed by evaporation of solvent
Sources & evidence
- ORD record
- ord-4aebc1ca12e94a7e8b4e1933cc1970b1
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04810792
Reaction notes
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